


Private Lessons With Mr. Winchester

by darkstiel (momstiel)



Series: SPN Kink Meme [1]
Category: Supernatural
Genre: Alternate Universe - High School, Alternate Universe - Student/Teacher, Anal Fingering, Anal Sex, Begging, Bottom Castiel, Cock Rings, Crying Castiel, Dubcon if you squint, High School Student Castiel, M/M, One Shot, Orgasm Control, Orgasm Delay/Denial, Rimming, Shota Castiel, Student Castiel, Teacher Sam, Teacher-Student Relationship, Teasing, Top Sam, Underage Castiel
Language: English
Status: Completed
Published: 2017-08-15
Updated: 2017-08-15
Packaged: 2018-12-15 18:40:13
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,652
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11811933
Author URL: https://archiveofourown.org/users/momstiel/pseuds/darkstiel
Summary: Castiel was usually a good boy… keyword, "usually".He needs private lessons and Sam knows how to get results.





	Private Lessons With Mr. Winchester

**Author's Note:**

> Based off of this prompt :  
>  http://spnkink-meme.livejournal.com/126067.html?thread=44028531#t44028531 
> 
> !! Warning !! 
> 
> This fic features a fourteen year old student Castiel having sexy times with his older teacher Sam 
> 
> Please read the tags first. :)

Castiel was usually a good boy… keyword,  _ usually _ . Ever since he started puberty, he spent more time than he wanted to admit thinking about sex. It was just around the time where he started to discover the world of pleasure (and his brother, Gabriel’s, porn stash). Cas wasn’t happy with himself, wanting to remain in the mindset of an innocent child. However, that wasn’t the case; his little buddy had different plans… time consuming plans. Most of the time the young Novak preferred to spend his evenings attending to his erections than to those pesky Algebra problems. Yet, alas, with such little time or interest dedicated to school work, Cas’s life was altering. 

 

It wasn’t long before his grades fell, and his teacher, Mr. Winchester, was quick to notice. Not being one to tolerate failure in his classroom, he decided to get in contact with his student’s guardian to suggest tutoring.  

 

Thus it was set up, every other day he was due to spend an hour after school let out until his grades improved. Castiel didn’t overly fancy this arrangement, but he was in no place to argue. So here he stood at the door of Sam Winchester’s classroom. It felt weird walking into the vacant room, Cas being so used to the area being full of chattering ninth graders. 

  
“Castiel, step in.” Mr. Winchester insisted, tapping a pen against the open lesson plans on his desk. He pushed glasses up the bridge of his nose, looking over the approaching scholar who was heeding his words. “Feel free to take a seat up near the front.” 

 

Obediently, Cas went up to the front and took a seat at a desk directly in front of his teacher’s. There was a few moments of silence as Sam scanned over a mess of scattered notes. However, it was abruptly cut short by the man slamming aside all of the papers. Castiel jumped a tiny bit by the sudden action, but didn’t question his instructor. 

 

“You’re fourteen, correct?” Sam asked, hazel eyes locking onto wide blue ones.

 

“Uh, yes.” Castiel scrambled to answer, wondering how Mr. Winchester’s question was relevant. A tiny, interested grin appeared on the tall man’s lips. 

 

“Okay.” Mr. Winchester replied, standing up and walking out from behind his desk. He walked around, going over to the front of Cas’s. “So, Cas, tell me what’s the deal with you lately?” 

 

Castiel opened his mouth as if he was going to respond but quickly shut it, blush rising to his cheeks. He didn’t want to admit that instead of dedicating one hundred percent of his evening studying for the midterm, he spent time researching BDSM online. “Uh, distractions I guess, Mr. Winchester.” 

 

“Distractions?” Sam asked, clearly unsurprised by his pupil’s answer. He pulled up a chair and sat down right by Castiel. “What kind of distractions?” The teacher prompted, a tiny grin on his lips. 

 

Instantly the fourteen year old scratched his neck awkwardly, attempting to form some kind of lie. “Like TV and stuff. The normal.” Castiel played his teacher’s inquiry off, not wanting to get the truth. Mr. Winchester seemed to be a calm and understanding person, but he knew that there was certain things that he just had to keep to himself. 

 

“Castiel…” Mr. Winchester dragged out the boy’s name in a deep way that caused his spine to tingle. “I think we both know that’s not the truth,” Sam accused calmly, crossing his arms. “Tell me the truth, I won’t be mad. I just want to help you.” 

 

Averting his eyes from the prompting professor, Cas stared down at his lap. “I already told you…. TV.” He insisted slowly, not sure what else he could say. “And maybe electronics.” 

 

Sam narrowed his eyes a tiny bit, little crinkles forming around his hazel eyes. “I told you to be honest, Castiel.” Even though he remained a calm demeanour, Cas could tell that Mr. Winchester was getting a little bit more irritated and pushing. “Is it your family?” Castiel shook his head, seeming a tiny bit surprised that Mr. Winchester would think the fault would lay in his household. “As you said earlier, you’re fourteen… I’m only left to assume that the only thing between you and your schoolwork is your teenage libido.” 

 

Instantly Cas became silent, unsure how to respond to his teacher’s correct allegations. “Uh.” He was dumbfounded, surprised that Mr. Winchester had gone in for the kill, passing all boundaries. 

 

“Don’t lie.” Sam warned, eyes sticking on his student. “Tell me the truth, and there will be no consequences.” Mr. Winchester claimed, continuing his pursuit for his student’s honesty. “Is that the reason why your grades are taking the hit?” 

 

“Yeah.” Cas whispered, barely audible. Nevertheless, he could tell that Mr. Winchester heard his response, a tiny grin on the teacher’s face. He sat still and silently as the older man leaned in, placing his lips tauntingly close to his student’s ear. 

  
“We might as well fix that problem then.” Mr. Winchester’s breath tickled Castiel’s skin and he felt another tingle shoot up his spine. The ninth grader wasn’t sure what his teacher planned to do, but his palms were starting to sweat because of the way that his instructor was talking. 

 

Without any hesitation, Sam put a hand on top of his student’s crotch. Instantly blush ran across Castiel’s face as he desperately tried to ignore the way his cock twitched in interest. “We’ve got to get you to get used to this little guy being hard while you’re doing homework… there’s only way to do that.” He paused, noticing the way that the dick responded. “Remove your pants.” 

 

The color red had made itself home on the boy’s cheeks. He knew that the right thing to do was stop and report his teacher’s perverted methods… but for some reason, he couldn’t bring himself to run out of the room. Instead, he found himself being slowly undressed by his professor. By the time that Mr. Winchester had removed Castiel’s pants, the fourteen year old felt his semi-erect cock pushing against the soft fabric of his underwear. “You seem eager.” Sam pointed out, but Cas made no effort to give him a reply. 

 

Not being faint-hearted, Sam continued on and discarded the boy’s clothing until the student was left naked. “Let’s do this.” The teacher suggested, going over to his desk, pulling out a cock ring, and coming back. He placed the ring around the base of Castiel’s semi-erect penis. “This will prevent you from coming prematurely, and it will strengthen your ability to concentrate with an erection.” 

 

Castiel shivered at the feeling of the cold ring, but his cock stirred up in fascination. He knew what the item was, guilty of watching orgasm controlled porn before. While he was adjusting to the feeling, he failed to notice Mr. Winchester heading back to his own quarters until a paper was plopped down on the desk in front of him. “Sit down, and try to fill this out. I want to see what you know.” 

 

Somewhat surprised and a little disappointed in the lack of attention to his erection, Castiel slowly sat down. Right now he didn’t want to do his work, he wanted to relieve himself. Sam watched as the boy began to half-heartedly put his name at the top of the page. 

 

Mr. Winchester watched for a little bit, eyes on his student’s raised prick. “Focus, Castiel.” He instructed before deciding to raise the heat a little bit. Going back to the drawers of his desk, he pulled out some lube. It was evident that Cas was confused on why Sam had such items handy, but he didn’t have time to think about it until he felt a lubed finger enter his ass. 

 

Instantly he grew tense, not used to an intrusion in his hole. For a few moments he just sat still, lost in the feeling of a finger popping in and out of him. “Castiel!” Sam reminded and instantly the blue eyed boy picked his pencil up again and started looking at the first problem. 

 

It felt like an eternity to Cas as he finished a problem with a finger exploring his insides. Sam inserted a second finger causing the boy to gasp in surprise. Instead of losing himself in the feeling, he continued to work on the second problem. Reaching up to Castiel’s front side, two fingers still working in and out of his ass, Sam began to tickle the underside of Cas’s balls. It took everything the ninth grader had to not moan, but he couldn’t help but thrust forward at the feeling. 

 

“Mr. W-Winchester…” Cas whined as he felt a wet finger explore along the underside of his erect cock. “Please…” He whimpered. “Can’t I do these problems l-later?” The boy asked, the simulation too much already. If it wasn’t for the damn cock ring keeping him from exploding, he knew that he would have already came. Now, his mind was clouded with lust and want. It was so hard to focus on the problem he had already re-read three times.

 

“I won’t stop until you finish your set of problems. Don’t rush, they need to be correct.” Sam responded, putting in another finger! Cas’s knees went to jelly when he felt three fingers rubbing against his inner walls. It hurt a little at first, but he was started to get use to the pleasure. “Come on, Castiel.” Mr. Winchester prompted. 

 

Biting his lip, the boy shakily finished the second problem. He even showed his work on the margin of the page, desperate for his release. It was only ten problems, but he knew that it could take him up to an hour to finish them. For a torturously long period, Mr. Winchester was teasing and simulation his hole, his balls, and his cock. “Eight more problems.” The teacher reminded, glancing over the boy’s shoulder. 

 

“Y-yeah…” Castiel whimpered, eyes widening when he felt hands leave his desperate lower regions. For a few seconds he was confused as to why Mr. Winchester stopped, but it all made sense when he noticed that his professor’s hands had went to his own pants, which he was working his way out of. All Cas wanted to do was stare as Sam stripped, revealing a huge erection. Mouth watering a tiny bit, the ninth grader turned back to his paper. He prayed to god that the second that he finished his problems he’d get fucked out of his mind and cum in the process. Very slowly and reluctantly, the boy finished his third algebraic problem. 

 

“Stand up.” Mr. Winchester instructed, causing Cas to blink but slowly stand up. The older man slipped into Castiel’s seat before grabbing his students by his hips and putting him on his lap. The ninth grader felt his skin burning up, not use to such of a sensation. He felt the man’s length teasing his hole, rubbing against his soft flesh. 

“Please….” Cas whined, desperate for any kind of attention. He tried to push back on the teacher’s erect cock but Mr. Winchester didn’t let him. Shaking as he went onto his fourth problem, Cas kept thrusting his hips forward, cock hitting the tip of the desk. As he fell back after each thrust, his ass was met with the warmth of his teacher’s erection. The teasing was dastardly, and he felt such of a strong urge to release right then and there. “Please!” He cried out, whining and rubbing into Mr. Winchester. 

 

“Get to your sixth problem.” Sam insisted, deciding to tease his whimpering and writhing student even more. He grabbed his own erection and began to flick it back and forth, rimming around Castiel’s puckered and clenching hole. Then, he pulled Cas back more, letting the student sit on his length that was now in between the boy’s thighs. His cock nestled against his pupil’s hot and pulsating balls. 

Castiel endured this torture, whining and begging for his teacher’s erection in his ass until he reached and finished the dread sixth problem. His eyes were hooded a little, not sure if he was able to handle this much longer. “Please! Fuck me! Let me cum! Please!” The boy glanced down at his own erection, watching the cock ring. Deciding to be devious, he tried to discreetly reach down and remove it. 

 

However, his approach came to a sudden halt when Sam noticed and pushed Castiel’s hands away from the young cock. “I won’t fuck you if you remove that.” He warned, grabbing his own erection and placing it into Cas’s clenching hole. 

 

Instantly the student whined and pushed back, sending the firm length deeper into his ass. He winced for a second, not used to the feeling. It hurt a little bit, but with each passing moment the pleasure was gaining more control. Desperately he began to fuck himself on Sam’s cock, tears rising at his eyes. He started problem seven with blurred vision, but Mr. Winchester began to wipe away the tears from his overwhelmed student’s eyes. 

 

“I’ll start moving when you finish problem eight.” Mr. Winchester promised, pleased with all of Castiel’s previous correct problems. The boy definitely knew his stuff, if he actually took the time to concentrate on them. 

 

“O-okay…” Cas whined in response, crying and begging still. He finished the seventh problem, hard dick still in his ass. Part of Castiel just wanted to pass out, rip the cock ring off of himself, and just go and sit down on Mr. Winchester’s dick whether the teacher liked it or not. But Castiel was a good boy, mostly. A part of him wanted to please the man, showing him that he was a golden student… and that he wasn’t just another delinquent! 

 

As he finished the eighth problem, almost on cue, Mr. Winchester’s hips began to snap forward into him. Castiel let out a huge moan, throwing his head back. His cock pulsated, wanting to release but that damn ring still preventing him from letting him do what he wanted to do. “Please!” Castiel cried out like a broken record, the thick dick buried deep into his gaping hole. “Fill me up! Fill me up! Let me cum!” 

 

“Get to problem ten.” Mr. Winchester commanded firmly, seeming to only acknowledge his student when Cas finishes a problem. Sam felt his own face flush, pushing into the now-open hole. He had always imagined fucking such of a beautiful young boy, and he couldn’t believe that he finally had one… begging and crying for him to spill all over inside of him. 

Completely overstimulated, Castiel raced in a focused manner to finish the next problem. Once he got to problem ten, his hand was shaking terribly but he was insistent on finishing. Just as he began to write down the solution, he moaned loudly when he felt Mr. Winchester hit his prostate. The hits kept on coming until he felt something hot and sticky filling up his hole. As he finished the very last number, done with the exercise, he felt warm hands working the cock ring off. 

 

All it took was for Mr. Winchester to lazily hit his prostate one more time and he came all over himself and the teacher’s hand. His head fell back onto the man’s chest behind him and he just inhaled and exhaled, taking in the best orgasm he had ever had. Completely spent, he just rested against his teacher, softening dick below him. Sam looked over his student’s paper, pleased to see that despite the distractions, the boy had gotten everything right. “Good job, Cas… you got an A+. I think your distractions should no longer be an issue..” 

 

Sleepily Cas glanced up at his teacher, biting his lip. “Can I still come to tutoring?” He asked. 

 

With a tiny grin on his lips, Sam nodded. “I think that can be arranged.” 


End file.
